Nice Guys Finish First

My name is Wyatt Gardner, and I’ve got a problem that plagues nice guys all over the world. The more attractive a girl is, the more likely I am to clam up, lose all confidence, and generally make a fool out of myself. Despite this little handicap, I’ve never been too lonely or sexually frustrated since, as my grandmother says, there are many fish in the sea. Plus, personality means a lot more to me than looks.

Last year, though, I met Alison, the woman of my dreams – funny, intelligent, a sparkling personality – who just happens to be a colossal babe.

I met her in Spanish class at San Diego State during my sophomore year. I used to spend a good chunk of the class period staring at her. For some reason I was obsessed with her back (which was nearly always bare) and the way her hair, tightly woven into a thousand tiny braids, settled on it. I remember wondering what it would be like to stare down at that perfect back while I fucked her from behind. One day, a month or so into the semester, she approached me after class and asked, in her mild Georgia accent, if I wanted to join her study group for the midterm exam.

I was excited to see Alison outside of class, but when I showed up at her apartment, that familiar relapse into shyness took hold. When she greeted me at the door her smile hit me like a ton of bricks. She was dressed to kill, with a tight, white tank top and equally tight jeans showing off her perfect, heart-shaped ass. A cross hung low on her neck, nestled in her bustline. (I’ve always thought there’s something really sexy about mixing sex and religion.)

True to form, I didn’t say more than ten words to Alison that night until, on my way out the door, I noticed a tear forming in her eye. Soon after, I was in her room listening to her heart-wrenching tale of woe caused by an unfaithful boyfriend.

At the time, I was more than happy to be her shoulder to cry on. At the end of the night, I got a nice big hug for it, which meant a good five seconds of her breasts smashed snug against my chest. I left her apartment feeling high on the possibilities. Her boyfriend was obviously a jerk, so it seemed I had arrived on the scene at just the right moment. My shyness around beautiful women wasn’t even turning out to be a problem, since she was doing most of the talking and I was getting points for just listening.

As it turned out, though, Alison often needed consolation, and mine was her favorite shoulder to cry on. She grew dependent on my shoulder, at the expense of the rest of me: namely my cock, which ached for her every time I laid eyes on her tight and pleasing form.

Alison and I grew closer as the weeks and months passed, but I found myself firmly stuck in the “just friends” category, that black hole of male sexual frustration. I can’t count the number of times I’ve helped her through her various crises with asshole boyfriends. Sometimes the crisis would revolve around her sex life, and I’d have to listen while she gave me all the lurid details. Every time the word “pussy” floated out of her sexy mouth I nearly died in frustration. Sometimes I wished she’d just find a gay guy to confide in.

Occasionally, I thought I picked up on a little bit of sexual energy between us, but it could easily have been wishful thinking. I never could get up the courage to tell her how I felt, though she’d have to be pretty stupid not to have noticed the many times when my glance would linger on her breasts for just a second more than was appropriate.

The worst part of all this was knowing that I could have made her so much happier than those muscle-bound, brainless jocks she was screwing. Despite her awesome body, creamy brown skin, and devastating smile, she was very sensitive and insecure at heart. None of the guys she dated were smart enough to understand this, so they’d always say the wrong thing and then not even know why their fine piece of ass wouldn’t speak to them anymore.

But Alison stuck to her pattern, alternating between jocks and plain old frat boys, which is why I was surprised one Friday when she called to invite me to her sorority invitational for 10 o’clock that night. It didn’t really qualify as a date, because I knew the girls were allowed to invite three people each. Still, she had never included me in anything like this before.

There were lots of excellent reasons to decline the invitation. For one, I’d have to cancel a date with a girl who’d made it abundantly clear that I’d wake up the next morning a “lucky” man. For another thing, I hadn’t been to any Greek event since I dropped out of my pledge class freshman year (after refusing to perform unnatural acts on a hoofed farm animal). The last, and probably best reason for not going was that I’d likely get an up-close and personal look at the lusty beginnings of another of Alison’s tragically stupid love affairs. She was in-between assholes at the moment.

In the end, the promise of seeing Alison fully decked out in all of her sorority girl glory made all of those reasons irrelevant. Also, I told myself this would be the night that I’d tell her how I felt, for better or worse.

I walked over to the sorority house at 10, but the bus to the nightclub had apparently already left! From the outside, the house looked completely dark and empty. I walked up to the front door and knocked, not really expecting an answer.

A split second after my knock sounded, however, the door opened and Alison was there. Since I happened to be looking down at the moment, the first thing I noticed was that she had no shoes on, and her toes were painted a lovely shade of pink. When I lifted my eyes, I saw that she wore one of those sheer silk robes that stop around mid-thigh. She had all her make-up on and looked like she had just stepped out of a Victoria’s Secret catalogue. The moonlight basked her body in an ethereal glow that made her look almost too sexy to be true.

Seeing my shocked expression, she whisked me inside, smiling and saying, “I thought it would be more fun to stay in. I hope you don’t mind.” There was a mischievous glint in her eye.

“Um, sure,” I replied. I couldn’t hide my confusion and surprise. After all, Alison was the sorority’s social president, and had spent weeks organizing the invitational. I couldn’t imagine what would make her want to stay at home.

“Actually, Wyatt, the truth is that I’m having some serious guy problems and, um, I was hoping I could talk them out with you. You’re always such a good listener.”

Now things started to make a bit of sense. But there was still definitely something weird going on. Why the make-up and the sexy robe, for example? And why didn’t she seem visibly upset about her “serious” guy problem? In any case, I’d find out in a minute. We settled onto the sofa in the common room and I waited for her latest sob story.

“So there’s this guy,” she began. “He’s so cute, and sweet, but he’s also a friend. I don’t know if I should tell him how sexually attracted I’ve become to him recently.”

As she talked she started to slowly move her hand over her leg, starting at her knee and moving steadily upward until it stopped just under her robe. She was curled up on her side with her legs tucked in close to her body. I was sitting on the same sofa but on the other end. Maybe six inches separated me from her nicely trimmed and painted toenails.

Meanwhile, the scent of her sexy perfume was starting to make my head swim. I was certain I’d smelled that perfume before, but not on her. The first stripper I’d ever seen, at a ritzy gentleman’s club in Los Angeles, had worn that scent. Her long, curly hair, luscious tits, and innocent, kissable mouth had drawn my attention while she was on stage doing a Catholic school-girl routine.

A few minutes after her performance she came over to where I sat with my friends and perched on my lap, offering a lap dance. I followed her to a private room where she informed me of all the “special” things she would do to me for just another twenty bucks. They all sounded pretty good to me. After about a half hour I’d dropped about 150, but felt like a million bucks.

The smell of the stripper’s perfume lingered in my memory for days afterward, but I’d eventually forgotten it. Until now, when the same vanilla scent wafted over to me from Alison’s side of the sofa, bringing back my memories of that night and making me aroused beyond belief. The fact that Alison’s nipples were showing through the sheer fabric of her robe made the sexual tension almost unbearable.

“Well, what do you think I should do?” Alison asked in an innocent tone of voice.

As I stammered and stumbled for an answer she switched positions, resting her back against the arm of the sofa and stretching her legs out fully so that her feet rested on my lap. Then, very slowly, she scooted one foot back along the couch, causing her knee to bend and her robe to open slightly, until I found myself staring right at her pussy, already glistening with moisture.

Believe it or not, part of me was still not convinced that this was a full-blown seduction. But then Alison jumped up from the couch, removed her robe entirely, and said, “Come on, let’s go for a swim!”

That put my mind at ease, and, hardly believing my luck, I followed her outside. The deck was secluded; entirely devoid of giggling sorority girls, who were probably now grinding sluttily and teasingly against the lower extremities of their horny dance partners.

But at this moment, only one sorority girl was on my mind; the one who was standing naked in a hot tub, her perky breasts exposed to the night air, beckoning me to join her. I stripped and obeyed, noticing that the tub was already warmed up and bubbling. She poured us wine from a bottle that she took from a pool-side cooler.

I was too overwhelmed by the situation to say much of anything, but before I had the chance to even open my mouth, Alison pushed me down to a sitting position and proceeded to straddle me. Smiling wickedly, she dipped a finger in her wine glass and offered it to me, taking away any need to speak. I gladly licked away the traces of wine on her finger. Meanwhile, my mind was racing with speculations about what was to come. I also couldn’t help but be aware of how close my fully erect cock was to her cunt as she straddled me.

Removing her finger, she leaned in close to me and I thought she was going to kiss my neck. Instead, she put her mouth right up to my ear and started whispering in her soft, sweet Southern twang.

“I know this is kind of a shock to you, Wy, since we’ve always just been friends. But I’ve seen the way you look at me sometimes, and I had a feeling you wouldn’t mind if I took our friendship to…another level. It took me a while to realize it, but you are exactly the kind of guy that I need and want. What I said before about your being a good listener is true, but you won’t have to hear me whine and moan about my guy problems anymore. Any moaning you hear from me from now on will definitely be of a different kind.”

Even if I had scripted it myself, her speech couldn’t have been more true to what I had fantasized about ever since I’d known her. While she spoke I just tried to take in the situation and enjoy the feeling of being seduced by the coolest chick I had ever met. But my ears were not the only part of my body that Alison was stimulating. About the time she was talking about taking our friendship to “another level,” she started softly pushing up against my cock and rubbing slowly back and forth. I could feel the folds of her pussy against the top of my shaft. After she finished talking, I was too distracted and aroused to reply in words. I kissed her soft mouth for a long minute, savoring the eroticism of the moment. Then I lifted her off my lap and hoisted her onto the lip of the hot tub so that only her calves and feet were submerged. Leaning back on her hands, she spread her legs and I went straight for her cunt, lapping up the juices that flowed freely now that she was out of the water.

“Oh, Wyatt, please don’t stop. That feels soooo good,” she moaned.

She ran her hands over her breasts and her hard brown nipples as I continued to lick along the curves of her outer lips. After a minute of this gentle teasing I started to pay attention to the sensitive area right around her clit. She was getting so wet that I had no trouble putting one and then two fingers inside her. I fucked her with my fingers, making her moan louder and louder. Finally I gave her what I knew she wanted, applying direct pressure with my tongue onto her clit. A few little flicks of the tongue was all it took. She shrieked with pleasure as her orgasm coursed through her body.

She kept her eyes closed and didn’t say anything for a minute. While she came back down to earth I hungrily lapped up some of her juices.

Then she said, “That was incredible, Wy. But I’m the one who should be doing the pleasuring tonight.”

I was more than happy to switch places with her so she could attend to my raging hard on. She slipped back into the hot tub and I took her spot on the lip of the tub, anxiously awaiting the blow job that I knew was coming. She surprised me, however, by bending down to softly kiss my stomach down around my hips. She used her tongue so expertly on my skin that I felt the sensations all over my body. I couldn’t even imagine what it would feel like once she got around to my cock.

But for the moment she continued her kissing, which was starting to drive me crazy with anticipation. After an eternity of teasing, she grasped my neglected cock in her hand and stroked it slowly, applying just the smallest amount of pressure. She did this almost casually, while the bulk of her attention remained on tasting the skin around my lower abs and waist. This combination of kissing and stroking was incredibly pleasurable, but after a while the night air started to feel cold against my cock. I wanted desperately to plunge inside her hot mouth.

Gradually, her kisses moved closer and closer to my throbbing member until finally she starting planting firm, wet kisses on the base of my shaft, working her way upward. With her hand she cupped my balls and gently caressed them. When she reached the head of my cock with her kisses, she suddenly became much more aggressive, which was exactly what I needed. In a flash, the cold night air on my cock was gone, replaced by hot breath and hot tongue. All of her teasing had been for a good purpose. When she took me all the way inside her, and the pleasure started to build to a level I’d never felt before, I became conscious of an irony. For more than a year now I had felt only jealousy and revulsion for Alison’s asshole boyfriends. But now, in the midst of this awesome blow job, I couldn’t help but be glad that she had had all those dicks to practice on!

She took me in and out of her mouth with slow and deliberate strokes, each time pausing briefly to massage the underside of my cock, just under the head. I could tell that the blow job was getting her almost as aroused as me, because she took one hand away from my shaft and started massaging her breasts and nipples.

After a couple of minutes of this exquisite treatment, I was almost ready to come. But just before the moment when climax became inevitable, she moved her hand from her breasts down underneath the water. The pressure on my cock lessened noticeably and I knew she was becoming lost in her own pleasure. She took me out of her mouth entirely and buried her head in my lap, moaning and then biting my skin. Soon she spasmed and let out a sigh of release, and then had me back inside her mouth again, working more furiously than ever.

“Come, baby, come,” she moaned through her mouthful of cock.

Suddenly I was hit with the reality of the situation; the girl of my dreams begging me to shoot my sperm down her throat. This thought sent me over the edge, and powerful streams of come burst into her mouth. She swallowed twice but I still had more to go.

“Yeah, baby. Come all over me!” she said as I pulled out and shot my third and fourth streams of come onto her face and breasts.

My sperm stuck to her hair and her cheeks. Little rivers ran down her neck, in–between her breasts, and over her cross necklace.

She dragged me down into the hot tub again and kissed me hard. We swirled around a glob of sperm that remained on her tongue, until finally she swallowed it.

“You are amazing,” I told her.

“Hey, it takes two to tango,” she said, hopping out of the hot tub and reaching for a towel.

At this point, I couldn’t help but wonder if our night was through, or if she wanted me to fuck her. Not that I was in much of a hurry, since my spent cock needed a rest. But after I climbed out, Alison, still naked, bent over to pick up the cover for the hot tub, giving me an eyeful of ass and pussy. It definitely wouldn’t be long before I’d be ready to fuck the hell out of her, if she wanted to.

After helping Alison cover up the hot tub, she excused herself and went upstairs to clean up. I dressed and waited in the common room. In a minute she appeared on the stairs wearing a thigh-length t-shirt that would leave anyone wondering what, if anything, was underneath. She also carried a few DVDs as well as what looked to be a shoe box.

“Want to watch a movie?”

“Sure,” I said. “What’s in the box?”

“None of your business. Just go to the kitchen and make us some popcorn while I set up the movie.”

I found some popcorn in the pantry and popped it in the microwave. While I waited, I sneaked a peek back into the common room and saw Alison bent over the DVD player, exposing what she wore underneath the t-shirt: a bright red g-string and a tiny tattoo of a cross on her right ass cheek.

I felt like abandoning the popcorn and taking her right there from behind, but was able to restrain myself. Letting Alison set the agenda for the evening had worked out great so far, and I wasn’t about to mess with a good thing.

We settled onto the sofa with our popcorn, with Alison resting her head against my chest and my arm around her. The movie she’d picked was Coming to America. She wanted to put on something we’d both seen before, “just in case we don’t feel like watching the whole thing.”

After a minute a scene came on where Prince Akeem and one of his hot servant girls have some fun in the royal bathtub, which is more like a swimming pool. This of course reminded Alison and me of the great oral sex we’d just had in the hot tub.

When the royal bather popped her head out of the water and announced, “The royal penis is clean!” Alison gave my cock a little squeeze through my pants. I was already high on the feeling of having Alison see me as more than just a shoulder to cry on. But now I got the feeling that she wanted all of me. Her nipples were practically bursting through the t-shirt material, betraying her excitement. Her breathing started to get a little heavier and I noticed her eyes were closed, while she continued rubbing me.

Because she was cuddled in so close to me, I had easy access to all of her body. With my right hand I gently rubbed her hard nipples, and with my left I pulled her t-shirt up over her ass and started tracing my fingers along the line of her skimpy panties.

“Touch me,” she said, reaching down to pull her g-string to the side, uncovering her pussy. I couldn’t believe how wet she was. After only a few seconds of exploring her labia with my fingers she took my hand and pressed my index finger firmly against her clit, immediately starting to moan with pleasure.

Her body grew tense under the power of the sensations and she started to squirm all around the sofa, tightening her legs around my hand like a vice to heighten the pressure.

Under the circumstances she couldn’t exactly form complete sentences, but she managed to eek out a feeble, “Th…th…the box….”